A Rhinebeck Farmhouse Like No Other: Tucked at the corner of River Road, just five minutes from the village of Rhinebeck, 77 Upper Hook Road is the rare property that delivers on every promise — history, beauty, land, and livability, all in one. Built in 1830 and thoughtfully renovated, this charming farmhouse sits on 3.43 private acres. The original character has been carefully preserved and the kitchen and bathrooms have been brought to a standard of quiet perfection. The result is a home that feels both deeply rooted and entirely ready to live in. Mornings begin under the pergola with coffee and birdsong, looking out over garden beds and a lush, verdant lawn. The west-facing dining room catches the afternoon light beautifully — the kind of room that makes people linger at the table. Just beyond the barn, a productive organic raised-bed garden supplies the kitchen with the freshest of ingredients. The fireplace anchors the living room, ideal for fireside evenings after a home-cooked meal. A cozy den rounds out the interior with space to read, stream, or simply exhale. Outside, the grounds are as impressive as the house. A magnificent, sprawling Magnolia tree anchors the yard alongside mature specimen trees that have been growing here for generations. The original barn — massive in scale and full of possibility — awaits its next chapter: studio, workshop, entertaining space, or something entirely your own. A charming one-bedroom guest cottage with a generous living area and windowed kitchen is ready for visiting friends or as an income-producing rental. The cottage's zen living room features a vintage wood stove that sets the tone for slow, unhurried weekends for guests. Just five minutes from Rhinebeck Village, five minutes from the Rhinecliff station, and five minutes from Kingston and Red Hook, near Omega institute and Duchess County Fairgrounds, the location couldn't be better. Properties like this — where the history is real, the renovation is right, and the land is truly special — don't come along often. This is Rhinebeck living at its finest.
Single-familyProperty Type
1830Year Built
3.43 acresLot Size
$600Price/Sq.Ft.
1 garage spacesParking
Listing by Wendy Maitland• Atelier WM LLC
Bought with Non Non Member-MLS• Buyer Representation Office
NOTE: CONTRACT PENDING. This GEM of a renovated, vintage home built in 1830 sits on 3.43 acres of prime land 5 minutes from the village of Rhinebeck, just off of prestigious River Road. Immaculately maintained and in excellent condition, the historic details of the house have been preserved while the kitchen and bathrooms have been renovated to perfection. Live your country home dream while enjoying a fireside chat after a freshly cooked meal in your modern, gorgeous eat in kitchen. The property boasts a gracious yard with mature trees, including a blooming Magnolia tree of epic proportions. For anyone with an adventurous spirit, you may find your second dream home by renovating the stunning, massive original barn. The 1 bedroom guest house offers a generous living space and windowed kitchen for those visiting from out of town, or can be used as an income producing unit. This very special home is charm incarnate. Please email or text for showings, further information, or to schedule a call to discuss.,Below Grnd Sq Feet:700,Level 2 Desc:2 LARGE BEDROOMS, 1 SMALL BEDROOM, LOVELY BATHROOM,Unfinished Square Feet:400,AboveGrade:2000,ExteriorFeatures:Landscaped,FLOORING:Wood,InteriorFeatures:Gas Stove Connection,Gas Dryer Connection,ROOF:Asphalt Shingles,Heating:Central Heat,FOUNDATION:Stone,Concrete,OTHERROOMS:Breakfast Nook,Library/Study,Office/Computer Room,Sun Room,Accessory Apartment,Level 1 Desc:KITCHEN, DINING, LIVING, MEDIA ROOMS, SCREENED PORCH 1/2 BTH
HVCRMLS #20170226
Mar 13, 2017
Sold
$580,000
$215/sq ft
Jan 17, 2017
Listed
$595,000
$220/sq ft
A classic home with history, this 3 BR, 1.5 bath Rhinebeck eyebrow colonial was built 30 years before Abraham Lincoln was elected president! Preserved, restored, charming, stylish & in exceptional condition, this home has been maintained to a high level by its current owners. There are exceptional period details with beautiful floors, doors, wainscoting, built-ins, & a classic fireplace. Flooded with light, perfectly proportioned 1st floor rooms include a great EIK, DR, LR, & den. A private 548 SF guest house has its own driveway & the well preserved barn has three stalls & a 22 x 36 vaulted loft where barn dances were once held. There’s a wonderful screened porch, garage, & 3.4 surveyed acres, with open, level, useable land, gardens, stone walls, & ornamental, mature plantings. On a country road, this home is very close to Rhinebeck V, Bard, Omega and Amtrak. It is not to be missed!
Directions: From the traffic light in Rhinebeck head north on Montgomery Street, make a left turn at Mt. Rutsen Road, bear right at River Road, make a right onto Upper Hook Road, 77 is the first house on right.
County Or Parish: Dutchess County
Public facts
Beds: 3
Baths: 1.5
Sq. Ft.: 1,932
Stories: 2.0
Lot Size: 3 acres
Style: Other
Year Built: 1875
Year Renovated: 2015
County: Dutchess County
APN: 135089A00617100002348090000
Home facts updated by county records on Oct 16, 2026
Around this home
Schools
Chancellor Livingston Elementary School
Public PreK-5 • Assigned • 3.7mi
6/10
Bulkeley Middle School
Public 6-8 • Assigned • 3.3mi
10/10
Rhinebeck Senior High School
Public 9-12 • Assigned • 3.3mi
8/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
4/10 Heat Factor
7 days above 98° expected this year, 15 days in 30 years
4/10 Wind Factor
10% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Rhinebeck, NY • 12572
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Sun exposure
Try the sun simulator tool to see how light moves across the property at different times of day and year.
Provided by Shadowmap
Estimated sale price
$1.46M – $1.77M
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